The general procedure for the synthesis of tert-butyl 3-hydroxycyclohexylcarbamate from N-Boc-3-cyclohexanone amine was as follows: sodium borohydride (710 mg, 18.8 mmol, 2.0 eq.) was slowly added to a solution of tert-butyl 3-oxocyclohexylcarbamate (2.0 g, 9.38 mmol, 1.0 eq.) dissolved in methanol (20 mL) at 0 °C. The reaction mixture was stirred continuously for 14 hours at room temperature. Upon completion of the reaction, the reaction was quenched with deionized water (20 mL) followed by extraction with ethyl acetate (30 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product tert-butyl 3-hydroxycyclohexylcarbamate (2.0 g, yield: 100%).
